Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
  • C08K5/57—Organo-tin compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/37—Thiols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/37—Thiols
  • C08K5/372—Sulfides, e.g. R-(S)x-R'
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
  • C08K5/57—Organo-tin compounds
  • C08K5/58—Organo-tin compounds containing sulfur

Definitions

• mercaptides are the most versatile heat stabilizers (examples of uses of such mercaptides, which contain tin-mercaptide bonds therein, can be found in U.S. Pat. No. 4,255,320 and PCT International Patent Publication No. 97/25373). Sulfides are not very effective on their own, but are used synergistically with mercaptides. Chlorides are weak stabilizers (see R. D. Dworkin, Chapter 19 in J. Edenbaum, Handbook of Polymer Additives). However, they are used together with other stabilizers to improve early color (e.g., Tables XIV and XV in European Patent Publication No. 890,608).
• Free (unreacted) mercaptans are known to improve color hold when added to other tin stabilizers (see, for example, U.S. Pat. No. 4,701,486 and PCT Patent Publication No. WO 99/09094).
• Mercaptans, and some organic derivatives, together with metal-based heat stabilizers and/or Lewis acids, which include organotin chlorides, are reported to be heat stabilizers or improved heat stabilizers (European Patent Publication Nos. 890,608 and 945,484).
• compositions of the present invention which, unlike conventional organotin heat stabilizers, does not contain any organotin mercaptides, is as effective as one that does.
• the stabilizer composition of the present invention comprises the following three essential components: at least one organotin sulfide; at least one organotin chloride; and at least one free mercaptan.
• organotin sulfide that can be used herein is exemplified by either (or both) of the monoalkyltin sulfide and dialkyltin sulfide compounds that have the formulae (RSnS 1.5 ) 4 and (R 2 SnS) 3 , respectively, with R being an alkyl group of from one to about twelve carbon atoms, with the butyl group being especially preferred.
• This organotin sulfide component is present at from about 20% to about 45%, by weight of the three previously enumerated essential stabilizer components.
• organotin chloride that can be used herein is exemplified by either (or both) of the monoalkyltin trichloride and dialkyltin dichloride compounds that have the formulae RSnCl 3 and R 2 SnCl 2 , respectively, with R, again, being an alkyl group of from one to about twelve carbon atoms, with the butyl group being especially preferred.
• This organotin chloride component is present at from about 3% to about 20%, by weight of the three previously enumerated essential stabilizer components.
• the free mercaptan component of the stabilizer mixture is present in larger amount that the two previously described components (for example, at from about 30% to about 70%, by weight of the all three essential stabilizer components).
• the three general types that can be employed are from the following known classes: the “reverse ester” type; the mercaptoesters; and the alkyl mercaptans.
• the reverse ester-type is a reaction product, for example, of 2-mercaptoethanol (a preferred mercaptoalkanol reagent) and a carboxylic acid, such as tall oil fatty acids (producing, for example, 2-mercaptoethyl tallate), adipic acid (producing, for example, 2-mercaptoethyl adipate), and the like.
• 2-mercaptoethanol a preferred mercaptoalkanol reagent
• a carboxylic acid such as tall oil fatty acids (producing, for example, 2-mercaptoethyl tallate), adipic acid (producing, for example, 2-mercaptoethyl adipate), and the like.
• R is an alkylene group of up to about four carbon atoms in length (ethylene being preferred) and L is a ligand such as —OC(O)R′, where R′ is, for example, alkenyl of from about six to about twenty carbon atoms in length (as exemplified by tallate) or alkyl of from eight to twelve carbon atoms.
• Another class of compound useful herein are the conventional mercaptoesters, as exemplified by the reaction product of thioglycolic acid (also known as mercaptoacetic acid, HSCH 2 CO 2 H, and an alcohol, which is commonly 2-ethylhexanol or isooctanol.
• thioglycolic acid also known as mercaptoacetic acid, HSCH 2 CO 2 H
• an alcohol which is commonly 2-ethylhexanol or isooctanol.
• preferred species within this class are 2-ethylhexyl thioglycollate and isooctyl thioglycollate.
• R alkyl mercaptans
• the previously described three component stabilizer mixture which is adapted to be used in conventional polyvinyl chloride formulations, can be dissolved in a larger amount of solvent containing conventional additives, such as antioxidants, lubricants, and antistats.
• the control was Interstab T-4997, an organotin mercaptide/sulfide in diluents, also containing 10% tin, which is commercially available from Akzo Nobel.
• Formulation Weight % Poly(vinyl chloride), 225, Oxychem 100.0 Impact modifier, Paraloid KM334, Rohm & Haas 5.0 Processing aid, Paraloid K120N, Rohm & Haas 0.5 Calcium stearate, Norac 1.1 External lubricant, Rheolube 315S, Allied Chemical 1.1 Calcium carbonate, Omyacarb UFT, Omya 12.0 Titanium dioxide, R-960, DuPont 2.0 Heat stabilizer (either Interstab T-4997 1.1 or the product from Example 1) Dynamic Stability Evaluation

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 2001
  • 2001-11-27 AU AU2002217892A patent/AU2002217892A1/en not_active Abandoned
  • 2001-11-27 WO PCT/US2001/044325 patent/WO2002042369A1/fr not_active Ceased
  • 2001-11-27 US US10/432,111 patent/US7087193B2/en not_active Expired - Fee Related

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